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Two heterosexual male friends Ben (Duplass) and Andrew (Leonard) meet after having not seen each other for 10 years. During a party, they find themselves locked in a "mutual dare" situation engaging to make a gay pornographic film, including anal sex, as an "art project" between two straight guys and submit it to the HUMP! film festival. They do not decide yet who will penetrate whom. Ben tells Andrew that he will discuss the project with his wife Anna (Delmore). However, as Ben begins to describe the project to Anna, she reacts skeptically at the mere mention of amateur pornography. Ben finds himself lying to Anna; he talks about the project with only vague detail, telling her that he will likely act as a behind-the-scenes assistant to the hypothetical film crew.

Later, Anna finds herself alone with Andrew and suggests that they have a drink together in an effort to get to know one another. Now drunk, the two begin discussing Ben and Andrew's art project, Andrew assuming that Ben has completely informed Anna of their intentions. After Andrew bluntly reveals that Ben will potentially have a gay experience, Anna becomes upset and confused, confronting Ben personally. The next morning, Ben insists that he still wants to go through with the project, and Anna consents.

Ben and Andrew meet in a hotel, bringing a video camera. Their attempts to have sex are prolonged by lengthy discussions and frequent analyzing of how to approach the experience. Although they film themselves kissing each other on the mouth, and hugging each other in their underpants, neither Ben nor Andrew appear comfortable becoming completely naked, let alone having sex. The two continue to talk, not sure if either one will be able to achieve an erection, and begin to question the validity of their experiment as a work of art. Ben finally suggests that they call off the project, and the two laugh at the ridiculousness of the situation. Ben leaves the hotel, intending to apologize to Anna. Andrew prepares to leave shortly afterward, but not before reviewing the footage that the two have recorded.

Humpday received positive reviews from critics. It has an approval rating of 79% on Rotten Tomatoes, based on 136 reviews, and an average rating of 6.7 out of 10. The website's critical consensus states, "Observant and insightful, this indie comedy takes a different tack on the "bromance" but still makes a point without sermonizing."[5] On Metacritic, the film has a weighted average score of 74 out of 100, based on 25 critics, indicating "generally favorable reviews".[6]

It has been categorized by some reviewers as part of the mumblecore movement in indie cinema.[7]